


Big Bad Wolf

by Piper_Halliwell1979



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Blow Jobs, Bottom Dean, Butt Plugs, Charlie Lives, Charlie Ships It, Charlie walks in on them, Confessions, Cosplay, Dean in Panties, First Kiss, Hand Jobs, Kinky sex, M/M, Naive Castiel, Oral Sex, Panty Kink, Roleplay, Sam Ships It, Sex Toys, Top Castiel, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2017-01-20
Updated: 2017-01-20
Packaged: 2018-09-18 18:25:44
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 2
Words: 2,441
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9397508
Author URL: https://archiveofourown.org/users/Piper_Halliwell1979/pseuds/Piper_Halliwell1979
Summary: Cas innocently orders a piece to complete his cosplay and it turns out to be a sex toy. Confessions are made as Dean explains it to him and it leads to kinky roleplay.





	1. Chapter 1

**Author's Note:**

  * For [SPNgreeneyes](https://archiveofourown.org/users/SPNgreeneyes/gifts).



“What the hell did you order?” Dean shook the plain brown package he picked up from their post office box. He noticed it was addressed to ‘Castiel Winchester’. 

 

“Charlie insisted on taking me to one of her conventions and told me I needed a costume to participate. I’ve already sewn the rest but needed to order the last piece.”

 

“Well alrighty then.” Dean pitched the box in the back of the Impala and they drove home. He was curious but knowing Charlie she'd convinced Cas to dress up as some obscure character he’d never even heard of. And Cas was likely to show him later anyway.

 

He was correct.

 

Later that evening Dean and Sam's game watching time was interrupted by a fur covered former angel holding the now opened mystery box. Sam kept his poker face whilst Dean blushed and cleared his throat nervously.

 

“I need some assistance. I can't seem to figure out how to attach this tail.” He tipped the box to show the brothers and that was enough to make Sam lose his composure. The fluffy tail was attached to a decent sized black butt plug.

 

“You um...you wanna field this one, Dean? It's more your area of expertise than mine.” Sam stared his brother down. He didn't bother fighting back the grin.

 

If looks could kill, Sam would have a thousand daggers in his face from Dean’s hard expression. “First of all, fuck you. Second of all...I’m not doing this in front of you. Come on, Cas. I’ll explain it in my room.”

 

_ Fucking Sasquatch. Confide in a guy and he teases me...well, I’d do the same to him. Whatever. Not cool, Sammy. _

 

Cas still looked confused. “I lose the effect of the Big Bad Wolf without the tail, Dean. And I don't have time to order something else. Charlie is Red Riding Hood.” He plucked the tail from the box and tried to hand it to Dean.

 

Dean sank down on the side of his bed and scrubbed his face. “Okay, how do I explain this? Um...you bought a sex toy, Cas.” He hoped that registered anything with wolf boy.

 

“How does one derive pleasure from this?” He furrowed his brow and inspected the piece further. 

 

_ I’m really going to have to do this.  _ “It’s a fancy butt plug. You use it to keep your ass stretched for anal sex or some people use it after to keep the jizz inside. That tail is for even kinkier sex where somebody pretends to be a wolf getting fucked or a wolf fucking somebody else. I don't kink shame. As long as both parties are consenting adults...whatever blows your skirt up, man.”

 

Cas pondered this information over and seemingly became more enlightened. “You do seem quite knowledgeable on the subject. Is that why Sam suggested you explain it to me?”

 

_ Oh Jesus, we’re doing this. We’re going to talk about this. _ “Sam was implying that I would know more about this because I enjoy anal sex. Like, receiving it.” Dean sucked in his breath and held it in wait for a response.

 

“Oh? I wasn't aware you had that sexual proclivity. I haven't seen you with a male companion.”

 

_ Great. Now for the bonus round.  _ “I actually haven't slept with a guy like that. I’ve done some pretty kinky things with women. Do you remember...no you wouldn't. I was with this girl, Rhonda. She um...she made me try on her panties and then she played around back there and I wound up with her vibrator in my ass. Came so hard I saw double.” He couldn’t help but smile at that nearly twenty year old memory.

 

“So it's a ‘kink’ of yours and not related to your sexual orientation?” Cas might have actually looked a little disappointed.

 

_ Well add this conversation to the long list of why my ass is going back to hell. “ _ I didn't say that. It just made me less afraid of letting it happen if I met the right guy I wanted to do it with. So far I've scratched the itch with...you know...toys. And that's how Sam found out and for all the confessions I'm making today that story ain’t one of them. Capische?”

 

“I capische.” Cas sat beside Dean on the bed. “You could have told me all this before. I would never judge you. It would be hypocritical of me.”

 

_ Wait, what?! “ _ You need to share something with me now, Cas?”

 

“I indulged in your porn on the computer. My human body keeps getting erections and if they get painful I...I masturbate. I find the men more stimulating than the women. I find the animated stuff disturbing but that is your business.”

 

Dean was possibly blushing the deepest red he ever had at the moment. Not at all where he thought the day was heading when he started errand running with his best friend.

 

“Okay. So we both get hot looking at guys. Nothing wrong with that.” Dean hesitated. “Think you’ll ever act on that? Get a boyfriend?”

 

Cas cast his eyes down to the floor. “I’ve only had strong emotions toward one man.”

 

About a billion butterflies tried to escape Dean's stomach at once. “Yeah, me too. Never thought he’d think of me that way. Always considered the guy too good for me anyway.”  _ If he's talking about Sam I swear I’m ganking myself on the spot and going straight to hell. _

 

“Dean? May I kiss you?” Cas’ voice trembled with nerves. His gaze hadn't left the floor. A warm hand found his chin and lifted. Soft lips pressed to his in a short, chaste kiss. Now Cas was the one blushing.

  
Dean went in for another and found Cas open and receptive to something more passionate. They clung to each other for a few moments, heads swimming with hormone surges. “Cas?” Is Charlie's costume here?”


	2. Chapter 2

All Dean found was the red hooded cape in Cas’ sewing room. Well, one of the smaller storage rooms he’d converted to his crafting area. He had a shit ton of yarn in there and various projects in different states of completion.

 

He returned to his bedroom with the cape and told Cas to lie back on the bed and close his eyes. He dug through one of the boxes tucked away in his closet and stripped out of his clothes. When he told Cas to open them he was standing at the foot of the bed wearing nothing but the cape and a pair of red satin panties with lace trim and a heart shape cut in the back. He’d bought them along with a box of chocolates before Valentine's Day as if they were for a lady friend.

 

Cas’ pupils fully dilated at the sight. Dean could tell they had a very positive effect on him. “You know the story of Little Red Riding Hood?”

 

Cas nodded wordlessly and licked his lips. He felt himself stiffen in arousal and shifted a little on the bed. Dean just smiled and stood there.

 

“My what big, beautiful eyes you have.”

 

“All the better to see you with,” Cas replied in character.

 

Dean climbed up on the bed. He crawled until he was hovering over Cas. “My what gorgeous lips you have.”

 

“All the better to kiss you with.” He reached a hand up behind Dean's neck to pull his face closer. He was welcomed into a wet, open kiss.

 

Dean plucked at the laces on the sides of Castiel's furry shorts. Once they were loosened he tugged them down to free Cas’ engorged member. “My what a big cock you have.”

 

“All the better to fuck you with.”

 

Dean shivered at the words. His panties got tighter and a small stain spread in the front from his own leaking dick. He kissed Cas again and smoothed his palm over the straining appendage. Cas moaned and writhed at his touch.

 

He wrapped his hand around it and gave a few loose strokes. He imagined Cas touching himself whilst sneaking and watching porn on his laptop. He scooted down a little on the bed and spread Cas’ legs so he could settle between them. He tilted Cas’ cock toward his lips and licked the bead of precum from his slit. Cas hissed and bucked his hips.

 

Dean knew his way around a dick. He’d given and received enough blowjobs in his life to fully please his lover. Cas was in for a real treat, but not too much. He had other plans than sucking him off.

 

He took in the head, wrapping his plump lips around it. Cas gasped at the new sensation and gripped the blanket on either side of him. Dean lowered down the shaft, struggling to take in even half of it. He’d have to rely on his hand to work the rest down to the base. He bobbed slowly and swirled his tongue around. He gave just enough suction to draw moans from Cas.

 

He cradled Cas’ full and heavy balls in his other hand, fondling them with a light touch. He felt the cock twitch in his mouth so he eased off. As much as he wanted to fully taste Cas he didn't want him coming quite yet.

 

Dean crawled up again, distracting Cas with his tongue in his mouth as he retrieved the bottle of Astroglide from his side table drawer. He deftly popped it open and squeezed some into his hand. He reached his slick fingers down to Cas’ cleft and teased the virgin hole.

 

“Dean!” Cas cried out. He felt the pressure of a fingertip against him and then the slight burn of the intrusion. Dean moved slowly until his middle finger was buried inside Cas’ velvet heat. He let Cas adjust before pulling it back and sliding it in again. This time Cas made a low sound in his throat.

 

Dean took his time pumping in and out. He tentatively introduced a second finger and found Cas very receptive. He scissored then, working Cas open enough to comfortably take the plug end of his tail. When he thought Cas was ready he pulled out and told him to roll over and get on all fours.

 

He poured a generous amount of the Astroglide on the toy and slicked it up with his hand. Cas flinched when the hard rubber pressed against him but relaxed and let Dean slowly push it inside until the base caught past his rim. More precum leaked and dropped onto the blanket.

 

“Now, Big Bad Wolf, I want you to prep me just like I did you,” Dean instructed. He turned around and presented himself. Cas changed position, moaning as the tip of the toy brushed his prostate.

 

He slid Dean’s red panties down to his knees. With the same care, he lubed up his own fingers and set about recreating what Dean had done to him. He started with one long finger and then another. Dean rocked back against him and begged for a third. Cas was a girth man so he needed more stretch to comfortably take him in.

 

Cas slicked up his cock and lined himself up with Dean's loosened hole. He pressed just enough for his head to pass the rim then eased the rest of the way in until he was fully sheathed in Dean's tight walls. He thought he may climax before he could make the first full stroke so he paused to let it settle.

 

“Move when you're ready, babe,” Dean told him. He was so full and having something warm and fleshy inside him felt better than any toy. Cas pulled back enough to just leave his head then snapped his hips to the hilt again.

 

It felt amazing. He remembered sex with the reaper and it was nothing as good as this. His sensations had been dulled by the condom he’d worn and he couldn’t find a good rhythm in his inexperience. Dean was working with him, meeting every thrust and making absolutely sinful noises of pleasure beneath him.

 

They went for several minutes like that before Cas felt his impending orgasm build back to the tipping point. He wrapped his arms around Dean's chest and pulled him back onto him. Dean happily bounced on his cock and took one of his hands to place on his own neglected dick. He guided Cas’ hand to stroke him in time with the thrusts.

 

“I’m almost there, Cas. I’m gonna...I’m...hgnnn...I’m coming, Cas. I’m coming!” He tightened around Cas and spilled his hot load over their fingers. A few seconds later he felt Cas twitch inside him and then the steady pulse as he was filled with cum.

 

Dean leaned back on Cas and turned his head for a sloppy kiss. He fell forward, losing the full sensation. He untied the cape and tossed it on the floor with his other clothes. He pulled up his panties and returned to the drawer for a travel packet of baby wipes to clean them up with.

 

He went around behind Cas and eased the tail plug out of him. Cas laid back on one of Dean’s pillows and pulled him close. Dean cuddled into him and nuzzled into the furry vest he was still wearing.

 

“Was that ‘kinky’, Dean?”

 

“Yeah, role-playing in the bedroom is definitely kinky. You like it?”

 

“It was rather enjoyable. I’m afraid I will have to decline Charlie's invitation now.”

 

“Why’s that?” Dean mumbled sleepily.

 

Cas huffed a small laugh. “Because I would have a painful erection all day thinking about what we did in these costumes.”

 

“Hmmm...good to know.” Dean said before drifting off.

 

***

 

“Hey, Dean, have you seen my...Oh my goddess! Nevermind. Didn't see anything.” Charlie startled them the next morning. She put a hand over her eyes and shuddered at the sight of her adoptive big brother naked in the arms of a half naked wolfman.

 

“Did you find your cape?” Sam asked when a traumatized Charlie joined him in the kitchen. “You okay?”

 

Charlie looked at him with wide eyes. “I don’t think I want it back. Dean sort of  _ borrowed _ it.”

 

Sam just scrunched his face in confusion. 

 

“You know, like maybe he got eaten by the Big Bad Wolf last night?” Her voice went up with the inflection.

 

“Oh god.” Sam pushed his half eaten bowl of cereal away. “They didn't. In costume?”

 

“Oh yeah. Glad I wasn't around to hear all the huffin’ and puffin’ last night.”

 

“Glad I fell asleep with headphones on. But hey, finally, right?”

  
“Yeah, finally.” Charlie agreed.


End file.
